N-(4-chlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide | 410542-87-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-(4-chlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide
• 英文别名: N-[(4-chlorophenyl)methyl]-8-hydroxy-1,6-naphthyridine-7-carboxamide
• CAS: 410542-87-9
• 化学式: C₁₆H₁₂ClN₃O₂
• 分子量: 313.743
• InChiKey: YZTWHZCMZKCCGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  75.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对氯苄胺 、 8-羟基-1,6-萘啶-7-羧酸乙酯 以 乙醇 为溶剂， 反应 18.0h， 以53%的产率得到N-(4-chlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide
  参考文献：
  名称：

  一系列具有有效体外抗利什曼原虫活性的 8-羟基萘啶的鉴定和优化：初始 SAR 和体内活性评估。

  摘要：

  内脏利什曼病 (VL) 是一种寄生虫感染，每年导致大约 26 000-65 000 人死亡。可用的治疗方法受到毒性、疗效可变和不合适的剂量选择等问题的阻碍。迫切需要新的治疗方法，这导致了被忽视疾病药物计划(DND i )、葛兰素史克 (GSK) 和邓迪大学之间的合作。8-羟基萘啶被确定为起点，早期化合物在 VL 小鼠模型中表现出较弱的功效，但受到葡萄糖醛酸化的阻碍。解决这个问题的努力导致开发了具有改善体外特征的化合物，但这些化合物在体内耐受性差. 对作用方式 (MoA) 的研究表明，活性是由二价金属阳离子的螯合驱动的，这种机制可能导致耐受性差。这突出了在早期研究表型活性系列的 MoA 和药代动力学的重要性。

  DOI：

  10.1021/acs.jmedchem.0c00705

文献信息

• Aza- and polyaza-naphthalenyl carboxamides useful as HIV integrase inhibitors
  申请人：——

  公开号：US20030055071A1

  公开（公告）日：2003-03-20

  Aza- and polyaza-naphthalenyl carboxamide derivatives including certain quinoline carboxamide and naphthyridine carboxamide derivatives are described. These compounds are inhibitors of HIV integrase and inhibitors of HIV replication, and are useful in the prevention or treatment of infection by HIV and the treatment of AIDS, as compounds or pharmaceutically acceptable salts, or as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of preventing, treating or delaying the onset of AIDS and methods of preventing or treating infection by HIV are also described.

  描述了包括某些喹啉羧酰胺和萘啉羧酰胺衍生物在内的氮杂萘基羧酰胺衍生物。这些化合物是HIV整合酶的抑制剂和HIV复制的抑制剂，可用于预防或治疗HIV感染和治疗艾滋病，作为化合物或药学上可接受的盐，或作为药物组合物中的成分，可选择与其他抗病毒药物、免疫调节剂、抗生素或疫苗组合使用。还描述了预防、治疗或延缓艾滋病发作的方法，以及预防或治疗HIV感染的方法。
• AZA- AND POLYAZA-NAPHTHALENYL CARBOXAMIDES USEFUL AS HIV INTEGRASE INHIBITORS
  申请人：Merck & Co., Inc.

  公开号：EP1326865A2

  公开（公告）日：2003-07-16
• US6921759B2
  申请人：——

  公开号：US6921759B2

  公开（公告）日：2005-07-26
• [EN] AZA- AND POLYAZA-NAPHTHALENYL CARBOXAMIDES USEFUL AS HIV INTEGRASE INHIBITORS<br/>[FR] AZA- ET POLYAZA-NAPHTHALENYL CARBOXAMIDES UTILES COMME INHIBITEURS DE L'INTEGRASE DU VIH
  申请人：MERCK & CO INC

  公开号：WO2002030930A2

  公开（公告）日：2002-04-18

  Aza- and polyaza-naphthalenyl carboxamide derivatives including certain quinoline carboxamide and naphthyridine carboxamide derivatives are described. These compounds are inhibitors of HIV integrase and inhibitors of HIV replication, and are useful in the prevention or treatment of infection by HIV and the treatment of AIDS, as compounds or pharmaceutically acceptable salts, or as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of preventing, treating or delaying the onset of AIDS and methods of preventing or treating infection by HIV are also described.
• [EN] AZA- AND POLYAZA-NAPHTHALENYL CARBOXAMIDES USEFUL AS HIV INTEGRASE INHIBITORS<br/>[FR] AZA-NAPHTALENYLE CARBOXAMIDES ET POLYAZA-NAPHTALENYLE CARBOXAMIDES UTILES EN TANT QU'INHIBITEURS DE L'INTEGRASE DU VIH
  申请人：MERCK & CO INC

  公开号：WO2002030931A2

  公开（公告）日：2002-04-18

  Aza- and polyaza-naphthalenyl carboxamide derivatives including certain quinoline carboxamide and naphthyridine carboxamide derivatives are described. These compounds are inhibitors of HIV integrase and inhibitors of HIV replication, and are useful in the prevention or treatment of infection by HIV and the treatment of AIDS, as compounds or pharmaceutically acceptable salts, or as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of preventing, treating or delaying the onset of AIDS and methods of preventing or treating infection by HIV are also described.